What I Learned From Interviewing 19 Millionaires

[Hey guys! Welcome Benjamin Davis from FromCentsToRetirement.com to the blog today. He’s been on an interesting journey lately hanging out with millionaires, and stops by to share some insight :) What a great way to soak up some knowledge, eh? Only costs you a cup of coffee!]

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While doing my PhD in Germany, I developed CFS/adrenal fatigue and I feared I could not work for much longer. I didn’t know much about finances or investing at the time – I had only invested in the stock market for a few years using very simple strategies.

As I educated myself, I decided that I needed a mentor. And I figured I would look for one in the area I wanted to retire in – mid-east Portugal, Europe.

If you’ve ever tried to get a mentor yourself, you know how difficult it can be at times. I asked many people whether they wanted to teach me how to get rich doing the same thing they did, but the answer came back negative over and over again. Until one person said:

Well I don’t have time for that, but I can tell you my story, maybe you’ll learn from it?

To this day I still remember how my brain started connecting the dots right then and there! I quickly shot back, “you’ve got time today?” and that was the beginning of something remarkable.

I went on to interview 19 self-made millionaires and multi-millionaires who taught me more than they’d ever know. I would invite them for a coffee, take out my notebook, and then ask them to tell me their stories. I would take notes like a professional reporter.

Finding them was a nightmare, however. At times I felt like I was wasting my time, and at others I felt like I had won the lottery and was learning things I would never have learned if I hadn’t talked to them.

I had all sorts of people interviewed. From cocky to humble, bankers to farmers. You’d expect to find a pattern in how they looked, but I didn’t. Some were dressed up, others looked close to homeless. Only a few told me their actual net-worth, but all of them, probably unconsciously, told me things that were instrumental for my own journey to wealth.

In this article, I will summarize 6 lessons I learned from them. I hope you can relate to them, and even more importantly I hope you apply some of them to your own life.

Lesson #1: Life Is About Way More Than Money

Antonio wanted to get rich desperately. He wanted to show his father how capable he was. He never told me what his father said that hurt him so much, but I could sense some revenge in the way he talked. He wanted to prove a point.

He told me his biggest mistake in life was barely living at all: “I barely had a life until today. I could never enjoy a dinner with my family or my wife’s cake. I could never stop thinking about improving my business and making more money. Even today, it seems that I don’t have enough – and that leaves me nervous.”

Antonio has a medium-sized retail business, which sells farming machinery. Back in the day, he used to run from small village to small village in order to find local farmers who would buy his equipment. Today, he stays at the business and sends his workforce to work. He looks like a concertmaster coordinating an orchestra.

He pays attention to every detail and has a huge hand-written database of clients and their needs. “This is worth gold” he told me, regarding his small notebook he started writing in long before e-mail was a thing. This guys knows marketing and the value of keeping a big record of clients, I thought.

The biggest lesson I learned from Antonio was that, even if it seems like it, life ain’t about the money. Not always, at least. Antonio ended up developing an inability to feel good when achieving something. He’s always wanting more. Even now that his business has expanded into 6 cities, he’s not satisfied. He never will be.

Lesson #2: Do What You Love, and The Money Will Come

Jose told me he never thought he could become a multi-millionaire selling tiles. “I never thought anyone could make a decent living doing this, even though I always loved home renovation and tiles.”

(If you’re thinking this is a strange thing to love, btw, know that Portugal has a history with tiles, bricks and stones. If you ever visit Lisbon you’ll understand why!)

“I wanted to become rich, so I started multiple businesses. I would move from business to business, looking for one that was really profitable, until I started selling homes.” But Jose never really made significant money selling homes. “The market was always very volatile, and crashes were terrible for us. This is not London or New York – it is a small city with a small market.”

A prospective buyer once told Jose he would buy the home he showed him, but only if he could find someone to renovate it for him on the cheap. He didn’t like the tiles in the kitchen and in the bathroom, but Jose knew no one he could refer to.

“I remember looking for days, asking all the other brokers in the company, but no one knew any business doing that.” Eventually that led to Jose setting up his own renovation business, and he started buying tiles in massive amounts for not only his own business but for other contractors too. Contractors who normally buy tiles in bigger cities, like Porto. It was a costly and slow process, but Jose saw an opportunity and jumped on it – eventually making more money on the tiles themselves than all the renovations!

He finally gave up the renovation business and focused solely on what he loved the most – selling tiles. Which eventually made a multi-millionaire. “Whenever anyone asks me what I do, I very proudly say that I sell tiles!”

Lesson #3: Taking Risks Is a Part of Wealth Building

“I mortgaged my house and I didn’t tell my wife. She would have had killed me if she knew!” I cannot name the guy who told me this as part of our agreement (he said I was the only one he ever told!), but for the sake of this article, I will call him “A.” A. was definitely the richest guy I interviewed, even though he didn’t reveal how much his net worth was. (He also didn’t pay for the coffees either. :-))

A. had a wonderful life. He had “the most beautiful girl in town!” and owned two paid-off homes by the age of 25 (and this was about 50 years ago. “No one had a house back then – only the rich!”) I asked him whether he was rich then, and he told me that he only became rich later on – after risking his two homes in a matter of months.

The story goes that this guy use to run a bike business. Back then, bikes were a true luxury and not many people had them. He would fix and sell bikes for the rich, but he “would never become one in the bike business.” Eventually, the real estate where he had his business was listed for sale. He decided to mortgage his home to buy it.

“It was not a smart move at first – my rent was fairly low so it didn’t make sense. I was starving for wealth – it was an impulse buy.” But a few months later, when he sold his business, he became highly aware of the value of that piece of real estate. “The guy who bought my business didn’t want to pay me dividends as part of our agreement, so instead I charged him a higher rent on the property I still owned – and he accepted!”

A. eventually realized he could replicate what he had just done, so he opened another bike business in a nearby town, bought the location from under it, and then listed both the business and the attached real estate for sale.

The word spread fast, and A. would sell his businesses for small losses, but more than recoup the money from the lucrative rents attached.

He’s still doing this today, decades later. Creating and franchising businesses to owners, who then agrees to move shops where A. wants them to: at his own locations! I remember this story every time I pass by a McDonald’s, as they have a pretty similar model as well.

(Interesting to note, A. still owns that first location he rented out and the bike business is also still there, now run by the second generation of the family.)

Lesson #4: Money Cannot Be Sitting In The Bank

This is also something I learned from A., as well as most of the other guys. All that A. does today in his holdings is making sure that liabilities are never too low and that money is always available. “I cringe if debt is too low – there must be something wrong!”

But what is really bad according to him is “money simply sitting in the bank.” He says there are 100 reasons to put it to work, and not one to hold onto it. I am not sure he didn’t overdo it there – as I think that holding onto cash can be an intelligent decision too. However, I totally understand why he said that, and that philosophy has worked quite well for him over time.

Most of the guys I interviewed told me that money is not made to stack up. “You can stack it at the top but it will vanish from the bottom” one of the millionaires said. These guys all lived through high inflation periods, so even those making more money than they could spend understand the power of inflation.

Lesson #5: Working For Someone Else Won’t Do The Trick

The only guy I interviewed who still worked for someone else was a banker. Yet, he had so many investments and had invested for so long that he could barely keep track of them all. When I asked him why he hasn’t left yet when he obviously can, he said “I like working at the bank, that is why I never quit. Plus, the benefits are great!”

He’s following lesson #2 :-)

All the other guys I interviewed, however, had businesses of their own. Though to be fair, finding millionaire employees would have been way more complicated to find so I didn’t even try – thinking I wouldn’t find many anyways. At the end of the day, most of the millionaires told me that they would have never accumulated so much wealth working for somebody else.

Manuel was the biggest advocate of self-employment among the 19. “I did $100k in one month, and almost $1 million total that year (this was probably in the 90s – my notes fall short on this, sorry!). Tell me a job where I could make that much? I only worked for somebody else when I was 14. I realized that it wasn’t for me when I had to deliver the profits at the end of the day and be given only a small portion of it. That made no sense to me…”

“Working for yourself is the best thing you can do. No boss, no rules and no limits.” Manuel went on to say. He even told me he “felt sorry” for some of his employees because they’ll never truly understand how much better off they’d be going out on their own.

I personally still work for a university where I do research part-time, so I see the merits of working for someone else, especially in what pertains to safety and comfort. However, I want to work entirely for myself after March 2018. My real estate portfolio should yield enough money to employ me by then :)

(Editor’s Note: I have to disagree here. While it may take longer getting wealthy working for someone else, it’s still very much do-able. Check out this 401(k) millionaire! You also have to keep in mind that not everyone has the personality or would be GOOD at running their own business. It takes a certain personality, along with a whole lot of risk. So if you know yourself well enough that a 9-5 is the place for you to be, then keep on rockin’ it and continue doing your thing. Self-employment can be amazing, but it’s not for everyone (nor is it the only path).)

Lesson #6: Educate Yourself Financially… and on Everything Else!

The first step I took towards becoming financially independent was educating myself by reading tons of books on personal finance. It surprised me that most of the millionaires I interviewed didn’t know who Robert Kiyosaki was (whose quote, “If you want to go somewhere, it is best to find someone who has already been there” led me to interview these people in the first place!), or even who Warren Buffett was.

But it’s obvious they educated themselves financially in other ways, like by reading the newspaper every day and learning through their own businesses on how to negotiate, make more money and ultimately scale. Most of them learned through trial and error.

I also noticed how most of them were really curious about how things worked in general. One asked me “How much do you think this café makes every year?” as we were sitting there in it. I didn’t know the answer, and neither did he (he was just trying to take an educated guess and fostering discussion) but it showed how his brain worked. During another interview, the guy started asking me so many questions about my own job that it seemed like I was the one being interviewed!

So basically, knowledge is key. And it seems that the rich understands this like nobody else.

I’m in the process of writing a big book on all these notes I’ve collected over the interviews, and if you’d like to be alerted when it comes out, be sure to sign up to my blog. It will include parts of all my interviews and many more lessons that I haven’t put here.

I agree with all of those lessons learned. We are working on our own side businesses and hope they take us to the next level, from multi-millionaires to multi-multi-multi-millionaires . Or maybe even Billionaires. Nothing wrong with dreaming big .

I find it interesting on the note that you have to be self-employed to become a millionaire. While that might be in most cases an easier way to become a millionaire. I think its possible if you have a good paying job and invest while working for someone!

While education can be a great tool to making money and becoming rich, I personally also think you can almost become “too educated” that the waters get muddy on what you are supposed to do. Having a clear focus is essential when consuming so much knowledge.

Mentoring is a lost art, sadly. I feel that older generations don’t realize the impact they can make on younger generations, by simply talking to them regularly.

I enjoy hearing advice and lessons from people that have done it, have made it to millionaire status. I think the best tip is to do what you love and the money will come. It may take a bit longer than you would like, but you are enjoying the journey and won’t mind.

Thanks for sharing! I am positive your book will be great, as this was an awesome start to it!

That was a fun one. I love how the one guy was adamant about having debt on his books. Of course, he means good debt: (aka leverage.) So listen all of you landlords who are hard charging to pay off the mortgage on your rentals: STOP and put that money into new rentals or new businesses instead. I also agree with not keeping cash piled up for some strange apocalyptic purpose. Get a HELOC or similar line of credit for that life boat. Keep your capital working!

Taking risks leads to rewards for the people who are successful, but not for the people who failed. When you only interview the people who are successful it seems like risk taking is the best strategy because you only interview those for whom the risks paid off and never talk to the people who lost money. It’s the same with stocks–non-diversified portfolios are more likely to beat the market by a lot but they are much more likely to underperform the market too. That’s the nature of risk.

I would love to interview suckers too, but those would probably not want to give me an interview. As J said, most millionaires also fail, so I’d rather interview millionaires and learn from their mistakes ;)

Wow! I’m a little envious of the opportunity you had to interview all of these people. I think some of the best things we can learn are from people who have walked before us. If we want to live rich, we have to find out what rich people do and model that. I loved the perspective the banker gave! He is still an employee working for someone else. Even as a millionaire he is content working because of his passion for his field. And THAT is why we should do what we love.

I understand your point, but the vast majority of the rich people I ever talked to told me they went down that road. Maybe you could eventually get famous playing the violin? Is that something that you TRULY love?

Holy moly, you’re everywhere!!! I just came from Mustard Money and you’re his guests post for the day too ha! I was like…”heyyy I just saw this guy over there!”

The story of A (#3) eesh that’s a little crazy for me. I can’t imagine not telling my spouse that. He got lucky I think. Real estate can turn sour quick if you’re over leveraged.

Point #5 is sadly true. And I mean sad because…well entrepreneurship is never easy and for introverts – even more so. You can clock in and out, the days will pass but if you want to spearhead something you have to run to catch up.

Thank you for writing up such great lessons! It’s awesome that you get to talk to so many millionaires! I don’t think I’ve ever met a millionaire before. It’s also nice that they agreed to meet with you!

I agree with you on all points mentioned above. However, number 2 is a bit tricky. My husband dreams of being a historian, but the pay prospects aren’t so great, so he ended up choosing another field. I think it would be great to do something you love that’s also potentially profitable.

The pay for actually being a historian may not be high, but you could always parlay that into a bunch of other things too I’d imagine? Speaking, publishing books, etc? I would have never guessed you could make money blogging and now there’s like a million ways to convert this “resume” into more income streams… Never know what can happen :)

Even in small, not so sexy markets, you can make tons of money. You remember the owner of Scrub Daddy when he first came to shark tank? That guy is a multi-millionaire today. What he loves? Sponges! :D

Couldn’t agree more with your comments J$, running a business is not for everyone. It certainly is a proven way to build wealth but it’s highly risky and it’s not the only way.

Having worked in both a large company for 10+ years and run my own businesses I can say that each has their pro’s and con’s and depending on the type of person you are one is going to fit better than the other.

“Check the box” on lesson #2 before going to lesson #5. If you don’t love running your own business then you’ll never make any money.

Hey Ben – Interesting read! I have spent some time in Portugal so I know what you mean when you said it was hard to find your millionaires. They hold wealth close to the chest! I really loved Jose’s story and being able to see it come full circle to do what he loves. We need more people in the world to be able to live out their passions – happy people breed happy people. :) Thanks for sharing!!

I love that they talk about the value of lifelong learning. I’ve never heard someone getting rich from sitting on the couch and repeating the same thing, day after day. I think you can naturally build wealth if you LIVE your life.

Loved this! Learning from the stories of others is something I love to do as well, I’ve interviewed a bunch of breadwinning, six figure, and/or millionaire moms on my site for just this reason. Stories are a fun and powerful way to learn. I’m not surprised that most of the people you talked to are business owners, the Millionaire Next Door found that was very common among self-made millionaires.

I definitely agree with the “Money Cannot Be Sitting In The Bank” philosophy. Depending on how you are using your money and how you invest. I borrow money to invest in the real estate and stock market. Hence, my money is not working for me if I am paying interest on my loans and I get almost next to nothing on the money that sits in my savings account.

For me, I either use the extra money to pay off my investment loan or use it to further invest. It may be difficult to manage your cash flow at the beginning, but eventually, this process will become easier as you gain more experience.

I love this so much! The lessons are great. I do disagree with the self employed lesson, only because my husband and I are employed by others and just recently hit the $1 million mark! I am 38 (turning 39 this month!) and he is 40. I think it is definitely possible if you are dedicated to it. I did start a side business two years ago as well, but that doesn’t net me all that much yet. Soon! Maybe I will start blogging, who knows. lol

#5 hits home for me the most. Working for someone else, unless you are a c-level exec you will never be rich. The only exception I can see to this rule is 2 people both making 150K – 200K each, It would reasonably easy to become a millionaire at that level so long as expenses were kept in control.

Personally as a business owner my compensation increased by $7K a month last year. There is no non-commission based job in existence where this would occur working for the man. Once I get enough for a decent down payment on a small building or small home I would like to go that route as well. Its been a source of anxiety for me only really having one source of income. If I am going to make this a forever thing I need to diversify.

Great points on owning your own business. I do think it’s possible to hit a million with even just one person making the numbers you mentioned. It might take longer as an employee to become a millionaire, but it will happen (as you mentioned, assuming costs are under control and savings are invested).

Learning all the time (especially in “non-traditional” ways) is the key I’m taking away. Sometimes you learn by failing at a business. Sometimes you learn by reading the paper and asking interesting people good questions.

This was so great, and what a cool experience to sit down and hear personal stories from so many millionaires. I liked #6 about educating yourself and how passionate, wealthy people’s minds work. My father owned a business with one business partner. When they sold it while I was in high school, his business partner retired but my father will likely have to work into his 60s. Why? They looked at money and investing differently.

I was always interested in building wealth, so spent a lot of time with my dad’s business partner. An honorary uncle. Once, when I was 13 or 14, we went out to lunch and passed a street performer. My uncle asked me, “How much do you think he makes in a year?” We actually ended up grabbing sandwiches and watching the performer for a whole hour, trying to estimate how much cash he was getting in his bucket. Then we sat down and made rough estimates on how many shows he could do a day, how many days a year we thought he worked, etc. We came up with $60-$65K a year!

After that, I can’t walk into a business or see any kind of money venture without trying to estimate how profitable it is. I guess that is one reason why I went into investing, where I get to learn about new businesses every day!

Great lessons. All make total sense outside of one. #5 is completely wrong.

There are plenty self-made millionaires who are employees of others, 4.6 million households according to studies done in 2017. There are dozens at the company I work for alone. Maybe these aren’t all 8 and 9 figure people, but they’re millionaires nevertheless. I’ve done both self-employment and working for someone else, and personally I find it much less stressful to have the structure, guidance, support, ability to leave work at work, and security of an employer.

I agree it’s tough to reach “buy an island” type money working for someone else, but you can certainly visit plenty of islands for as long as you want in retirement if you plan correctly.

Side gigs are all well and good for these folks though to help maximize retirement savings, myself included.

Thanks for sharing about your findings from interviewing all of those millionaires. The wisdom is priceless. The purpose of having money is to give your family a better life and to help others. It was interesting reading all of the different perspectives.

Man that must have been a great experience interviewing that many wealthy people and getting to know the lessons they went through to be millionaires.
Probably the lesson that stuck out to me is to educate yourself. You have always be willing to learn in order build up your knowledge and see what others have experienced so you try get something out of it.
Great job Ben!!

My motto is you can find mentors in strange places. One of my Life Advisors is an old school PF blogger who has done amazing things and lives a wonderful life – we met through money blogging. One was a C-Suite exec most of his adult life in the comics industry – we met because I’m a comics nerd. One is in her 70s, born during the war and lived an amazing life and career and in her retirement she does more than any of us does in a week :) – we met through my husband’s hobby.

They have all played key roles in reaching me to negotiate and navigate my career but not one of them work or worked in my industry. Knowledge and experience is powerful stuff so you don’t have to limit yourself to just the people who work in the same field as you.

And I disagree with the notion that self employment is the only way to millionaireship because I started my career making less than $30k a year and we managed to join the double comma club with only minimal side hustles. We’ve both seen the dark side of self employment so we’re under no illusions that self employment is the Golden Ticket. It can be if you have the right idea, the right drive, the right luck, and the right fallback. But it’s really not for everyone.

The key is knowing that your money earned from traditional employment needs to work for you too, it can’t just be you working!

This was such a good post and great read. Cannot agree more with all of the above lessons especially on be willing to take risks and always try to educate yourself. Things around us are constantly changing and we need to change with them.

Thank you for taking the time to share your findings and lessons with us. It is truly greatly appreciated.

It’s interesting to note that you ended your post with curiosity. It’s something I’m definitely trying to develop more of in my life–asking people questions about what they do, wondering how much income/expenses a local business has. I always learn a ton from these interviews. Thanks so much for the great article!

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I, J. Money, only claim the thoughts from my head. I am not a banker, CPA, money manager or anything else of that sort. Please seek a professional for any "real" advice. More info: privacy & disclosure page